US4912210A - Process for the preparation of (cyclo)aliphatic uretediones - Google Patents
Process for the preparation of (cyclo)aliphatic uretediones Download PDFInfo
- Publication number
- US4912210A US4912210A US07/244,355 US24435588A US4912210A US 4912210 A US4912210 A US 4912210A US 24435588 A US24435588 A US 24435588A US 4912210 A US4912210 A US 4912210A
- Authority
- US
- United States
- Prior art keywords
- diisocyanate
- uretedione
- dimerization
- reaction mixture
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 title description 6
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- 238000001704 evaporation Methods 0.000 claims abstract description 12
- 230000008020 evaporation Effects 0.000 claims abstract description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 14
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 13
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 13
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 claims description 3
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 150000003222 pyridines Chemical class 0.000 description 9
- -1 amino-substituted phosphines Chemical class 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- ODKLEQPZOCJQMT-UHFFFAOYSA-N n,n-diethylpyridin-4-amine Chemical compound CCN(CC)C1=CC=NC=C1 ODKLEQPZOCJQMT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000010517 secondary reaction Methods 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
- MTPBUCCXRGSDCR-UHFFFAOYSA-N 4-piperidin-1-ylpyridine Chemical compound C1CCCCN1C1=CC=NC=C1 MTPBUCCXRGSDCR-UHFFFAOYSA-N 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Chemical group 0.000 description 2
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical class PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 239000003183 carcinogenic agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000447 dimerizing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 150000003928 4-aminopyridines Chemical class 0.000 description 1
- QJWQYVJVCXMTJP-UHFFFAOYSA-N 4-pyridin-4-ylmorpholine Chemical compound C1COCCN1C1=CC=NC=C1 QJWQYVJVCXMTJP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- JEDHEXUPBRMUMB-UHFFFAOYSA-N n,n-dimethylpyridin-3-amine Chemical compound CN(C)C1=CC=CN=C1 JEDHEXUPBRMUMB-UHFFFAOYSA-N 0.000 description 1
- FDIOSTIIZGWENY-UHFFFAOYSA-N n-[bis(diethylamino)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(N(CC)CC)N(CC)CC FDIOSTIIZGWENY-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
Definitions
- the invention is related to an improved process for the preparation of largely isocyanurate-free uretediones from (cyclo)aliphatic diisocyanates.
- uretediones can be processed into light-fast, single and two component polyurethane paints.
- isocyanurates is undesired in a number of applications since, as well-known, they are trifunctional and have a tendency to form crosslinkages. In practice an admixture of more than 0.5% is regarded as undesirable.
- uretediones can be prepared in the presence of specific catalysts through dimerization of isocyanates.
- antimony pentafluoride, trialkylphosphines, amino-substituted phosphines, imidazoles, guanidines, and pyridines have been proposed.
- a process is known from FR-PS No. 15 32 054 in which tertiary phosphines or boron trifluoride are added as dimerization catalysts. However, they catalyze not only the dimerization but also to a significant degree also the trimerization of isocyanates. In addition to this, due to its high corrosiveness, boron trifluoride can be added only when specific protective measures are taken.
- 1,2-Dimethylimidazole is an excellent dimerization catalyst for aromatic isocyanates (cf. Synthesis 1975, p. 463 ff.).
- this catalyst is clearly less selective. For example, when benzyl isocyanate is added, a mixture of 24% isocyanurate and only 76% uretedione is obtained.
- the uretedione of the isophorone diisocyanate is prepared in the presence of an organic phosphorus-nitrogen-catalyst by means of dimerization of monomers and then distilled in a thin-layer evaporator.
- the uretediones remain in the distillation residue while the unconverted monomers with the majority of the added catalyst are collected as distillate, which is recycled into the process.
- Tris-(N,N-dimethylamino)-phosphine (PTD) is designated as the preferred catalyst.
- Uretediones, which were produced in the presence of PTD contain typically 1% isocyanurate, 1% monomers, and 0.01-0.1% catalyst.
- dimerization catalysts are also known from the literature. For example, in the JP-AS No. 71/37 503 the dimerization of 2,4-toluylene diisocyanate with cyclic amidines such as 1,8-diazabicyclo[5.4.0]undec-7-en is described. Experiments conducted by the Applicant show that (cyclo)aliphatic diisocyanates cannot be dimerized with this catalyst (see reference example A). Apparently the well-known, low reactivity of these diisocyanates is inadequate to facilitate a reaction.
- the object of DE-PS No. 10 81 895 is a process for the preparation of N,N-diaryluretediones and triarylisocyanurate acid esters through di- or trimerization of aromatic isocyanates.
- Pyridines containing a substituent in the 3- or 4-position and of a specified basicity are used as catalysts.
- 4-aminopyridines that are substituted by means of alkyl groups are mentioned. According to this process, it is apparently possible to obtain uretediones, isocyanurates or their mixtures, depending on the quantity of the catalyst, the reaction temperature, and type of solvent that is used.
- the catalyst be added in a quantity ranging from 0.005 to 15%, with respect to the weight of the isocyanate added, the mixture be reacted at the lowest temperature possible, and an inert organic solvent be used in which the uretedione dissolves poorly.
- one object of the present invention is to provide a process for catalytic preparation of (cyclo)aliphatic uretediones with more than 99% purity, which is independent of the use of expensive and potentially carcinogen aminophosphines.
- Isophorone diisocyanate is preferred as a diisocyanate.
- the substituted pyridine in particular p-dimethylaminopyridine, is added in a quantity ranging from 0.05 to 10% by weight, preferably from 0.2 to 5% by weight.
- Dimerization is preferably performed at a temperature between 0° to 100° C., the thin-layer evaporation depending on the attached vacuum ranging from 0.1 to 20 mbar at a temperature from 150° to 190° C. The distillate of the thin-layer evaporation can be recycled again. It is preferable that the dimerization be performed in the presence of an inert protective gas to provide an anhydrous atmosphere.
- (cyclo)aliphatic is meant aliphatic and cycloaliphatic diisocyanates having 6 to 15 carbon atoms, preferably 8 to 12 carbon atoms.
- hexamethylene diisocyanate, dodecamethylene diisocyanate and bis(4-isocyanatocyclohexyl)-methane and their mixtures are suitable for use as the diisocyanates.
- Preferred aliphatic diisocyanates are 2-methylpentamethylene diisocyanate, as well as 2,2,4- and 2,4,4-trimethylhexamethylene diisocyanate.
- isophorone diisocyanate is preferred.
- the pyridine used as dimerization catalyst has the general formula: ##STR4##
- R 1 and R 2 denote, independently of one another, an alkyl group having 1 to 4 carbon atoms or together with the neighboring nitrogen atom form a pyrrolidine, piperidine, or morpholine ring. Excellent results are achieved with p-pyrrolidinopyridine (see Tables 4 and 5). However, due to their better availability, 4dimethylaminopyridine and/or 4-diethylaminopyridine are preferred as catalysts.
- the catalyst is added in a quantity ranging from 0.5 to 10%, in particular from 0.2 to 5%, with respect to the parts by weight of the diisocyanate added.
- the dimerization can be performed in the presence of solvents, which are inert with respect to diisocyanates.
- solvents which are inert with respect to diisocyanates.
- hexane, toluene, xylene, chlorobenzene and their mixtures are suitable.
- the reaction temperature normally ranges from about 0° to 100° C., preferably from about 20° to 80° C. It is advantageous to perform the dimerization in the presence of a protective inert gas atmosphere such as nitrogen, argon, etc. to provide substantially androus conditions.
- a protective inert gas atmosphere such as nitrogen, argon, etc. to provide substantially androus conditions.
- the reaction may be carried out at normal atmospheric pressure.
- the reaction times generally range from 1 to 5 days, and depend primarily on the concentration of the catalyst.
- the reaction feedstock is subjected directly to a vacuum thin-layer evaporation.
- the temperature is set, in particular, at 180° C. and the pressure is set at 0.55 mbar in the preevaporator.
- the temperature is, in particular, 165° C. and the pressure is 0.05 mbar.
- the dwell time in the pre-evaporator and the main evaporator is then approximately 1 minute respectively.
- the distillate comprises monomer diisocyanate and catalyst. It is preferable to recycle the distillate to the dimerization process.
- the degree of dimerization was determined using the NCO number and the course of the reaction was observed with the aid of the NCO number.
- the NCO number is determined according to the method described in Houben-Weyl "Methoden der Organischen Chemie", Vol. 14/2, Stuttgart (1963), p. 85.
- the isocyanurate content in the reaction product is determined qualitatively using IR spectroscopy and quantitatively by determining the thermal value of NCO.
- the sample is boiled in dichlorobenzene for 2 hours. Then the NCO number is determined in the conventional manner.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3739549 | 1987-11-21 | ||
| DE3739549A DE3739549C2 (de) | 1987-11-21 | 1987-11-21 | Verfahren zur Herstellung (cyclo)aliphatischer Uretdione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4912210A true US4912210A (en) | 1990-03-27 |
Family
ID=6341000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/244,355 Expired - Lifetime US4912210A (en) | 1987-11-21 | 1988-09-15 | Process for the preparation of (cyclo)aliphatic uretediones |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4912210A (fr) |
| EP (1) | EP0317744B1 (fr) |
| JP (1) | JP2601530B2 (fr) |
| AT (1) | ATE97659T1 (fr) |
| CA (1) | CA1274835A (fr) |
| DE (2) | DE3739549C2 (fr) |
Cited By (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143994A (en) * | 1990-09-20 | 1992-09-01 | Bayer Aktiengesellschaft | Polyisocyanate mixture, a process for its preparation and its use in polyurethane coating compositions |
| US5258508A (en) * | 1991-06-15 | 1993-11-02 | Bayer Aktiengesellschaft | Process for the preparation of oligomeric polyisocyanates and their use |
| US5315004A (en) * | 1993-04-05 | 1994-05-24 | Olin Corporation | Process for producing uretidione dimers of isocyanates using catalysts which are bound to inorganic matrices |
| US5449775A (en) * | 1992-06-05 | 1995-09-12 | Basf Aktiengesellschaft | Imidazole group containing polymeric catalysts their preparation, and their use in the preparation of isocyanates containing uretdione groups |
| US5461020A (en) * | 1993-04-05 | 1995-10-24 | Olin Corporation | Dialkyl amino pyridine catalysts which are bound to inorganic matrices and processes for their preparation |
| US5484916A (en) * | 1992-06-05 | 1996-01-16 | Basf Aktiengesellschaft | Process for the preparation of isocyanates containing uretdione groups by using imidazole group containing polymeric catalysts |
| US5565527A (en) * | 1992-06-05 | 1996-10-15 | Basf Aktiengesellschaft | Polymeric, catalytically active compounds, their preparation, and their use as catalysts in the preparation of polyisocyanates containing uretdione groups |
| EP0789017A1 (fr) * | 1996-01-30 | 1997-08-13 | Bayer Ag | Uretdiondiisocyanates |
| US5773550A (en) * | 1996-02-19 | 1998-06-30 | Huels Aktiengesellschaft | Polyaddition product containing isocyanurate groups and uretdione groups, and a process for preparing same |
| US5882544A (en) * | 1996-12-20 | 1999-03-16 | Bayer Aktiengesellschaft | Polycyclic iminooxadiazinediones from (cyclo)aliphatic 1,4-diisocyanates |
| US5912314A (en) * | 1996-03-16 | 1999-06-15 | Huels Aktiengesellschaft | Reaction product of mixed uretdiones and a disecondary diamine |
| US6043332A (en) * | 1997-08-13 | 2000-03-28 | Bayer Aktiengesellschaft | Process for the production of light-colored uretdione polyisocyanates |
| US6319311B1 (en) | 1998-04-24 | 2001-11-20 | Osi Specialties, Inc. | Powder coatings employing silyl carbamates |
| US20030013872A1 (en) * | 2001-05-14 | 2003-01-16 | Hans-Josef Laas | Method of dimerizing isophorone diisocyanate |
| US6534568B1 (en) | 1998-04-24 | 2003-03-18 | Crompton Corporation | Powder coating or adhesives employing silanes or silane treated fillers |
| US6624301B1 (en) * | 1995-03-25 | 2003-09-23 | Degussa Ag | Process for the preparation of (cyclo)aliphatic uretdiones of improved color quality |
| US20040049028A1 (en) * | 2002-07-04 | 2004-03-11 | Hans-Josef Laas | Isocyanates containing uretdione groups |
| US20040106789A1 (en) * | 2002-11-25 | 2004-06-03 | Frank Richter | Preparation of polyisocyanates containing uretdione groups |
| US20040110915A1 (en) * | 2002-12-05 | 2004-06-10 | Frank Richter | Low-monomer-content polyisocyanates containing uretdione groups |
| US20050003206A1 (en) * | 2003-05-03 | 2005-01-06 | Degussa Ag | Solid polyurethane powder coating compositions containing uretdione groups that are hardenable at low temperatures |
| US20050033006A1 (en) * | 2003-08-07 | 2005-02-10 | Jurgen Kocher | New catalysts for selective isocyanate dimerization |
| US20050113551A1 (en) * | 2003-11-21 | 2005-05-26 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups |
| US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
| US20050239956A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
| US7030266B2 (en) | 2001-05-14 | 2006-04-18 | Bayer Aktiengesellschaft | Method for producing polyisocyanates |
| US20060173152A1 (en) * | 2005-01-21 | 2006-08-03 | Bayer Materialscience Ag | Uretdione formation in solution |
| US20070270565A1 (en) * | 2006-05-18 | 2007-11-22 | Bayer Materialscience Ag | New Catalysts for selective isocyanate dimerization |
| US20080265201A1 (en) * | 2007-04-26 | 2008-10-30 | Degussa Gmbh | Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups |
| DE102007022789A1 (de) | 2007-04-26 | 2008-10-30 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, Uretdiongruppen aufweisende Polyurethanzusammensetzungen enthaltend Polymere auf der Basis von sekundären OH-Gruppen tragenden Polyolen |
| DE102007057057A1 (de) | 2007-11-27 | 2009-05-28 | Evonik Degussa Gmbh | Uretdiongruppen haltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und haftungsverbessernde Harze enthalten |
| US20090143558A1 (en) * | 2007-12-04 | 2009-06-04 | Bayer Materialscience Ag | Preparation of uretdione polyisocyanates |
| DE102007061012A1 (de) | 2007-12-18 | 2009-06-25 | Evonik Degussa Gmbh | Dual Cure Formulierungen mit Uretdiongruppen haltigen Komponenten |
| DE102008007386A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
| DE102008002703A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten |
| US7709680B2 (en) | 2007-04-17 | 2010-05-04 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups using phosphine catalysts |
| WO2010108701A1 (fr) | 2009-03-24 | 2010-09-30 | Evonik Degussa Gmbh | Préimprégnés et corps moulés réalisés à partir desdits préimprégnés |
| WO2010108723A1 (fr) | 2009-03-24 | 2010-09-30 | Evonik Degussa Gmbh | Préimprégnés et corps moulés réalisés à basse température à partir desdits préimprégnés |
| DE102009002301A1 (de) | 2009-04-09 | 2010-10-14 | Evonik Degussa Gmbh | Verfahren zur Herstellung von monomerarmen 1:1 Addukten aus Hydroxyalkyl(meth)acrylaten und Diisocyanaten |
| DE102009027395A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Degussa Gmbh | Reaktive Derivate auf Basis Dianhydrohexitol basierender Isocyanate |
| DE102010029355A1 (de) | 2010-05-27 | 2011-12-01 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper |
| WO2011157507A1 (fr) | 2010-06-17 | 2011-12-22 | Evonik Degussa Gmbh | Demi-produit pour la fabrication d'éléments composites renforcés par des fibres sur la base de composés de polyuréthanne stables pendant le stockage |
| WO2012038203A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Préimprégnés à base d'une composition de polyuréthane stable au stockage, réactive ou hautement réactive |
| WO2012038200A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Préimprégnés à base d'une composition de polyuréthane stable au stockage, réactive ou hautement réactive |
| DE102010041256A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Prepregs auf der Basis lagerstabiler reaktiven oder hochreaktiven Polyurethanzusammensetzung mit fixierter Folie sowie die daraus hergestellten Composite-Bauteil |
| WO2012038105A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Procédé de fabrication de préimprégnés de polyuréthanne stables au stockage et corps moulés formés de ces préimprégnés à base d'une composition de polyuréthanne en solution |
| WO2012093006A1 (fr) | 2011-01-04 | 2012-07-12 | Evonik Degussa Gmbh | Produits semi-finis composites et pièces moulées produites à partir de ceux-ci ainsi que pièces moulées produites directement à base de (méth) acrylates fonctionnalisés par un hydroxy qui sont réticulés de manière duroplastique au moyen d'uretdiones |
| DE102011006163A1 (de) | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten |
| DE102012218081A1 (de) | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität |
| DE102013204124A1 (de) | 2013-03-11 | 2014-09-11 | Evonik Industries Ag | Composite-Halbzeuge und daraus hergestellte Formteile sowie direkt hergestellte Formteile auf Basis von hydroxyfunktionalisierten (Meth)Acrylaten und Uretdionen die mittels Strahlung duroplastisch vernetzt werden |
| DE102014208415A1 (de) | 2014-05-06 | 2015-11-12 | Evonik Degussa Gmbh | Herstellung eines auf Stahl und Polyurethan basierenden Faserverbundbauteils |
| DE102014208423A1 (de) | 2014-05-06 | 2015-11-12 | Evonik Degussa Gmbh | Herstellung eines auf Aluminium und Polyurethan basierenden Faserverbundbauteils |
| DE102014209183A1 (de) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Reaktive Zusammensetzung aus einer Uretdiongruppen haltigen Dispersion und Polyaminen |
| DE102014214130A1 (de) | 2014-07-21 | 2016-01-21 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten |
| EP2979851A1 (fr) | 2014-07-28 | 2016-02-03 | Evonik Degussa GmbH | Fabrication efficace de demi-produits et composants composites dans le cadre du procédé de pressage à froid utilisant des (méth)acrylates hydroxyfonctionnalisés réticulés par duroplastie à l'aide d'isocyanates ou d'uretdions |
| EP2993202A1 (fr) | 2014-09-08 | 2016-03-09 | Evonik Degussa GmbH | Demi-produits composites et pièces moulées en étant constituées ainsi que pièces moulées directement fabriquées à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdions réticulés par duroplastie |
| EP3124515A1 (fr) | 2015-07-28 | 2017-02-01 | Evonik Degussa GmbH | Dispersions reactives non aqueuses pour peintures, materiaux d'etancheite et adhesifs |
| EP3138685A1 (fr) | 2015-09-03 | 2017-03-08 | Evonik Degussa GmbH | Composant hybride dote d'un renfort local constitue d'un materiau en fibres composites a base de polyurethane, reticule en deux etapes |
| EP3330311A1 (fr) | 2016-12-02 | 2018-06-06 | Evonik Degussa GmbH | Préimprégné de monocomposant polyuréthane stable au stockage et corps moulés ainsi fabriqués à partir de ladite composition de polyuréthane |
| CN109574934A (zh) * | 2018-12-21 | 2019-04-05 | 六安科瑞达新型材料有限公司 | 一种脂肪族脲二酮的制备方法 |
| WO2019175714A1 (fr) | 2018-03-16 | 2019-09-19 | 3M Innovative Properties Company | Compositions, procédé de collage et assemblage |
| WO2019175709A1 (fr) | 2018-03-16 | 2019-09-19 | 3M Innovative Properties Company | Compositions, procédé de liaison et ensemble lié |
| EP3560971A1 (fr) | 2018-04-27 | 2019-10-30 | Evonik Degussa GmbH | Système à matrice hybride à deux composants de polyuréthanes et de polyméthacrylates destiné à la fabrication de demi-produits renforcés par des fibres courtes |
| EP3572446A1 (fr) | 2018-05-24 | 2019-11-27 | Evonik Degussa GmbH | Mélange réactif d'uretdiones et de catalyseurs |
| WO2020065456A1 (fr) | 2018-09-25 | 2020-04-02 | 3M Innovative Properties Company | Composition thermodurcissable en une partie |
| EP3929233A1 (fr) | 2020-06-25 | 2021-12-29 | Evonik Operations GmbH | Compositions de polyuréthane réactives |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3930670A1 (de) * | 1989-09-14 | 1991-03-28 | Basf Ag | Verfahren zur herstellung von uretdiongruppen aufweisenden polyisocyanaten |
| DE4406445C2 (de) * | 1994-02-28 | 2002-10-31 | Degussa | Verfahren zur Herstellung von uretdiongruppenhaltigen Polyadditionsprodukten und deren Verwendung in Polyurethan-Lacksystemen |
| DE4426131A1 (de) | 1994-07-22 | 1996-01-25 | Bayer Ag | Lichtechte, lösemittelfreie Polyurethan-Beschichtungsmittel und ihre Verwendung |
| DE19548250A1 (de) * | 1995-12-22 | 1997-06-26 | Huels Chemische Werke Ag | Verfahren zur Herstellung eines isocyanurathaltigen Uretdions aus Isophorondiisocyanat sowie das danach hergestellte Uretdion |
| DE19701714A1 (de) * | 1997-01-20 | 1998-07-23 | Huels Chemische Werke Ag | Verfahren zur Herstellung eines isocyanatfreien Uretdions des Isophorondiisocyanats |
| DE10346957A1 (de) | 2003-10-09 | 2005-05-04 | Degussa | Hochreaktive, flüssige uretdiongruppenhaltige Polyurenthansysteme, die bei niedriger Temperatur härtbar sind |
| DE102005060828A1 (de) | 2005-12-20 | 2007-06-28 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyadditionsverbindungen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1207673A (en) * | 1967-01-02 | 1970-10-07 | Ici Ltd | New isocyanate compounds and the use thereof |
| DE3420113A1 (de) * | 1984-05-30 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | Neue uretdiondiisocyanate, diese diisocyanate enthaltende polyisocyanatgemische, ein verfahren zu deren herstellung und ihre verwendung zur herstellung von polyurethankunststoffen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2683144A (en) * | 1951-10-02 | 1954-07-06 | Du Pont | Polymerization of isocyanates |
| US2643250A (en) * | 1951-11-16 | 1953-06-23 | Du Pont | Isocyanate dimers as color forming intermediates |
| DE1081895B (de) * | 1957-01-09 | 1960-05-19 | Ici Ltd | Verfahren zur Herstellung von N, N'-Diaryluretedionen und Triarylisocyanursaeureestern |
| GB944309A (en) * | 1961-06-16 | 1963-12-11 | Ici Ltd | Polymerisation of organic isocyanates |
| US3524834A (en) * | 1967-01-02 | 1970-08-18 | Ici Ltd | Cross-linkable composition of a thermoplastic polymer and a uretidione oligomer |
| DE2452390C2 (de) * | 1974-11-05 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von aromatischen Uretdiongruppen aufweisenden Polyisocyanaten |
| DE2502934A1 (de) * | 1975-01-24 | 1976-07-29 | Bayer Ag | Uretdiongruppen und endstaendige blockierte isocyanatgruppen aufweisende organische verbindungen |
| DE3030513A1 (de) * | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung eines isocyanuratfreien uretdions aus isophorondiisocyanat sowie das danach hergestellte uretdion |
-
1987
- 1987-11-21 DE DE3739549A patent/DE3739549C2/de not_active Expired - Fee Related
-
1988
- 1988-09-15 US US07/244,355 patent/US4912210A/en not_active Expired - Lifetime
- 1988-10-03 DE DE88116319T patent/DE3885859D1/de not_active Expired - Lifetime
- 1988-10-03 AT AT88116319T patent/ATE97659T1/de not_active IP Right Cessation
- 1988-10-03 EP EP88116319A patent/EP0317744B1/fr not_active Expired - Lifetime
- 1988-11-18 CA CA000583461A patent/CA1274835A/fr not_active Expired - Lifetime
- 1988-11-18 JP JP63290313A patent/JP2601530B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1207673A (en) * | 1967-01-02 | 1970-10-07 | Ici Ltd | New isocyanate compounds and the use thereof |
| DE3420113A1 (de) * | 1984-05-30 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | Neue uretdiondiisocyanate, diese diisocyanate enthaltende polyisocyanatgemische, ein verfahren zu deren herstellung und ihre verwendung zur herstellung von polyurethankunststoffen |
Cited By (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143994A (en) * | 1990-09-20 | 1992-09-01 | Bayer Aktiengesellschaft | Polyisocyanate mixture, a process for its preparation and its use in polyurethane coating compositions |
| US5258508A (en) * | 1991-06-15 | 1993-11-02 | Bayer Aktiengesellschaft | Process for the preparation of oligomeric polyisocyanates and their use |
| US5449775A (en) * | 1992-06-05 | 1995-09-12 | Basf Aktiengesellschaft | Imidazole group containing polymeric catalysts their preparation, and their use in the preparation of isocyanates containing uretdione groups |
| US5484916A (en) * | 1992-06-05 | 1996-01-16 | Basf Aktiengesellschaft | Process for the preparation of isocyanates containing uretdione groups by using imidazole group containing polymeric catalysts |
| US5565527A (en) * | 1992-06-05 | 1996-10-15 | Basf Aktiengesellschaft | Polymeric, catalytically active compounds, their preparation, and their use as catalysts in the preparation of polyisocyanates containing uretdione groups |
| US5637664A (en) * | 1992-06-05 | 1997-06-10 | Basf Aktiengesellschaft | Polymeric, catalytically active compounds, their preparation, and their use as catalysts in the preparation of polyisocyanates containing uretdione groups |
| US5315004A (en) * | 1993-04-05 | 1994-05-24 | Olin Corporation | Process for producing uretidione dimers of isocyanates using catalysts which are bound to inorganic matrices |
| US5461020A (en) * | 1993-04-05 | 1995-10-24 | Olin Corporation | Dialkyl amino pyridine catalysts which are bound to inorganic matrices and processes for their preparation |
| US6624301B1 (en) * | 1995-03-25 | 2003-09-23 | Degussa Ag | Process for the preparation of (cyclo)aliphatic uretdiones of improved color quality |
| EP0789017A1 (fr) * | 1996-01-30 | 1997-08-13 | Bayer Ag | Uretdiondiisocyanates |
| US5750629A (en) * | 1996-01-30 | 1998-05-12 | Bayer Aktiengesellschaft | Uretdione diisocyanates and a process for their production |
| US5773550A (en) * | 1996-02-19 | 1998-06-30 | Huels Aktiengesellschaft | Polyaddition product containing isocyanurate groups and uretdione groups, and a process for preparing same |
| US5912314A (en) * | 1996-03-16 | 1999-06-15 | Huels Aktiengesellschaft | Reaction product of mixed uretdiones and a disecondary diamine |
| US5882544A (en) * | 1996-12-20 | 1999-03-16 | Bayer Aktiengesellschaft | Polycyclic iminooxadiazinediones from (cyclo)aliphatic 1,4-diisocyanates |
| US6043332A (en) * | 1997-08-13 | 2000-03-28 | Bayer Aktiengesellschaft | Process for the production of light-colored uretdione polyisocyanates |
| US6319311B1 (en) | 1998-04-24 | 2001-11-20 | Osi Specialties, Inc. | Powder coatings employing silyl carbamates |
| US6534568B1 (en) | 1998-04-24 | 2003-03-18 | Crompton Corporation | Powder coating or adhesives employing silanes or silane treated fillers |
| US6797800B2 (en) | 2001-05-14 | 2004-09-28 | Bayer Aktiengesellschaft | Method of dimerizing isophorone diisocyanate |
| CN100509898C (zh) * | 2001-05-14 | 2009-07-08 | 拜尔公司 | 异佛尔酮二异氰酸酯二聚的方法 |
| US20030013872A1 (en) * | 2001-05-14 | 2003-01-16 | Hans-Josef Laas | Method of dimerizing isophorone diisocyanate |
| US7030266B2 (en) | 2001-05-14 | 2006-04-18 | Bayer Aktiengesellschaft | Method for producing polyisocyanates |
| US6987158B2 (en) | 2002-07-04 | 2006-01-17 | Bayer Aktiengesellschaft | Polyadducts containing uretidone groups |
| US20040059082A1 (en) * | 2002-07-04 | 2004-03-25 | Hans-Josef Laas | Polyadducts containing uretdione groups |
| US7098289B2 (en) | 2002-07-04 | 2006-08-29 | Bayer Aktiengesellschaft | Isocyanates containing uretdione groups |
| US20040049028A1 (en) * | 2002-07-04 | 2004-03-11 | Hans-Josef Laas | Isocyanates containing uretdione groups |
| US7067654B2 (en) | 2002-11-25 | 2006-06-27 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups |
| US20040106789A1 (en) * | 2002-11-25 | 2004-06-03 | Frank Richter | Preparation of polyisocyanates containing uretdione groups |
| US20040110915A1 (en) * | 2002-12-05 | 2004-06-10 | Frank Richter | Low-monomer-content polyisocyanates containing uretdione groups |
| US7572876B2 (en) | 2003-05-03 | 2009-08-11 | Evonik Degussa Gmbh | Solid polyurethane powder coating compositions containing uretdione groups that are hardenable at low temperatures |
| US20050003206A1 (en) * | 2003-05-03 | 2005-01-06 | Degussa Ag | Solid polyurethane powder coating compositions containing uretdione groups that are hardenable at low temperatures |
| US7317112B2 (en) | 2003-08-07 | 2008-01-08 | Bayer Materialscience Ag | Catalysts for selective isocyanate dimerization |
| US20050033006A1 (en) * | 2003-08-07 | 2005-02-10 | Jurgen Kocher | New catalysts for selective isocyanate dimerization |
| US20050113551A1 (en) * | 2003-11-21 | 2005-05-26 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups |
| US7151151B2 (en) | 2003-11-21 | 2006-12-19 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups |
| US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
| US20050239956A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
| US8058382B2 (en) | 2005-01-21 | 2011-11-15 | Bayer Materialscience Ag | Uretdione formation in solution |
| US20060173152A1 (en) * | 2005-01-21 | 2006-08-03 | Bayer Materialscience Ag | Uretdione formation in solution |
| US20070270565A1 (en) * | 2006-05-18 | 2007-11-22 | Bayer Materialscience Ag | New Catalysts for selective isocyanate dimerization |
| US7709680B2 (en) | 2007-04-17 | 2010-05-04 | Bayer Materialscience Ag | Preparation of polyisocyanates containing uretdione groups using phosphine catalysts |
| US20080265201A1 (en) * | 2007-04-26 | 2008-10-30 | Degussa Gmbh | Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups |
| DE102007022789A1 (de) | 2007-04-26 | 2008-10-30 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, Uretdiongruppen aufweisende Polyurethanzusammensetzungen enthaltend Polymere auf der Basis von sekundären OH-Gruppen tragenden Polyolen |
| DE102007057057A1 (de) | 2007-11-27 | 2009-05-28 | Evonik Degussa Gmbh | Uretdiongruppen haltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und haftungsverbessernde Harze enthalten |
| US8134014B2 (en) * | 2007-12-04 | 2012-03-13 | Bayer Materialscience Ag | Preparation of uretdione polyisocyanates |
| CN101450928B (zh) * | 2007-12-04 | 2014-01-29 | 拜尔材料科学股份公司 | 脲二酮聚异氰酸酯的制备 |
| US20090143558A1 (en) * | 2007-12-04 | 2009-06-04 | Bayer Materialscience Ag | Preparation of uretdione polyisocyanates |
| DE102007061012A1 (de) | 2007-12-18 | 2009-06-25 | Evonik Degussa Gmbh | Dual Cure Formulierungen mit Uretdiongruppen haltigen Komponenten |
| DE102008007386A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
| DE102008002703A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten |
| US8829146B2 (en) * | 2008-06-27 | 2014-09-09 | Evonik Degussa Gmbh | High-reactivity, uretdione-containing polyurethane compositions which comprise metal-free acetylacetonates |
| US20110039030A1 (en) * | 2008-06-27 | 2011-02-17 | Evonik Degussa Gmbh | High-reactivity polyurethane compositions containing uretdione groups and metal-free acetylacetonates |
| WO2010108701A1 (fr) | 2009-03-24 | 2010-09-30 | Evonik Degussa Gmbh | Préimprégnés et corps moulés réalisés à partir desdits préimprégnés |
| WO2010108723A1 (fr) | 2009-03-24 | 2010-09-30 | Evonik Degussa Gmbh | Préimprégnés et corps moulés réalisés à basse température à partir desdits préimprégnés |
| DE102009001806A1 (de) | 2009-03-24 | 2010-09-30 | Evonik Degussa Gmbh | Prepregs und daraus bei niedriger Temperatur hergestellte Formkörper |
| DE102009001793A1 (de) | 2009-03-24 | 2010-10-07 | Evonik Degussa Gmbh | Prepregs und daraus hergestellte Formkörper |
| DE102009002301A1 (de) | 2009-04-09 | 2010-10-14 | Evonik Degussa Gmbh | Verfahren zur Herstellung von monomerarmen 1:1 Addukten aus Hydroxyalkyl(meth)acrylaten und Diisocyanaten |
| WO2010115644A1 (fr) | 2009-04-09 | 2010-10-14 | Evonik Degussa Gmbh | Procédé de préparation d'adduits 1 : 1 à faible teneur en monomères, de (méth)acrylates d'hydroxyalkyle et de diisocyanates |
| DE102009027395A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Degussa Gmbh | Reaktive Derivate auf Basis Dianhydrohexitol basierender Isocyanate |
| DE102010029355A1 (de) | 2010-05-27 | 2011-12-01 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper |
| WO2011147688A1 (fr) | 2010-05-27 | 2011-12-01 | Evonik Degussa Gmbh | Procédé de préparation de pré-imprégnés de polyuréthane stables au stockage et corps moulés préparés à partir de ceux-ci |
| WO2011157507A1 (fr) | 2010-06-17 | 2011-12-22 | Evonik Degussa Gmbh | Demi-produit pour la fabrication d'éléments composites renforcés par des fibres sur la base de composés de polyuréthanne stables pendant le stockage |
| DE102010030233A1 (de) | 2010-06-17 | 2011-12-22 | Evonik Degussa Gmbh | Halbzeug für die Herstellung von Faserverbundbauteilen auf Basis von lagerstabilen Polyurethanzusammensetzungen |
| WO2012038200A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Préimprégnés à base d'une composition de polyuréthane stable au stockage, réactive ou hautement réactive |
| DE102010041256A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Prepregs auf der Basis lagerstabiler reaktiven oder hochreaktiven Polyurethanzusammensetzung mit fixierter Folie sowie die daraus hergestellten Composite-Bauteil |
| WO2012038201A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Préimprégnés à base d'une composition de polyuréthane stable au stockage, réactive ou hautement réactive, comportant une feuille fixée, et élément composite comportant ces préimprégnés |
| DE102010041247A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung |
| DE102010041243A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Prepregs auf der Basis lagerstabiler reaktiven oder hochreaktiven Polyurethanzusammensetzung |
| DE102010041239A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Prepregs auf der Basis lagerstabiler reaktiven oder hochreaktiven Polyurethanzusammensetzung |
| WO2012038105A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Procédé de fabrication de préimprégnés de polyuréthanne stables au stockage et corps moulés formés de ces préimprégnés à base d'une composition de polyuréthanne en solution |
| WO2012038203A1 (fr) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Préimprégnés à base d'une composition de polyuréthane stable au stockage, réactive ou hautement réactive |
| WO2012093006A1 (fr) | 2011-01-04 | 2012-07-12 | Evonik Degussa Gmbh | Produits semi-finis composites et pièces moulées produites à partir de ceux-ci ainsi que pièces moulées produites directement à base de (méth) acrylates fonctionnalisés par un hydroxy qui sont réticulés de manière duroplastique au moyen d'uretdiones |
| DE102011006163A1 (de) | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten |
| WO2012130672A1 (fr) | 2011-03-25 | 2012-10-04 | Evonik Degussa Gmbh | Pré-imprégnés de polyuréthane stables au stockage et corps moulés préparés à partir desdits pré-imprégnés à base d'une composition de polyuréthane contenant des composants en résine liquides |
| DE102012218081A1 (de) | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität |
| WO2014053269A1 (fr) | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Polyisocyanates hydrophiles stables au stockage |
| DE102013204124A1 (de) | 2013-03-11 | 2014-09-11 | Evonik Industries Ag | Composite-Halbzeuge und daraus hergestellte Formteile sowie direkt hergestellte Formteile auf Basis von hydroxyfunktionalisierten (Meth)Acrylaten und Uretdionen die mittels Strahlung duroplastisch vernetzt werden |
| WO2014139796A1 (fr) | 2013-03-11 | 2014-09-18 | Evonik Industries Ag | Semi-finis composites et pièces moulées produites en ces semi-finis, et pièces moulées produites directement, à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdiones, qui sont réticulés en duroplastiques par irradiation |
| DE102014208423A1 (de) | 2014-05-06 | 2015-11-12 | Evonik Degussa Gmbh | Herstellung eines auf Aluminium und Polyurethan basierenden Faserverbundbauteils |
| US9902096B2 (en) | 2014-05-06 | 2018-02-27 | Evonik Degussa Gmbh | Production of fibre composite component part based on aluminium and polyurethane |
| EP2946922A1 (fr) | 2014-05-06 | 2015-11-25 | Evonik Industries AG | Production d'un composant en composite de fibre à base d'acier et de polyuréthane |
| EP2946923A1 (fr) | 2014-05-06 | 2015-11-25 | Evonik Industries AG | Production d'un composant composite en fibres à base d'aluminium et de polyuréthane |
| US9902095B2 (en) | 2014-05-06 | 2018-02-27 | Evonik Degussa Gmbh | Production of fibre composite component part based on steel and polyurethane |
| DE102014208415A1 (de) | 2014-05-06 | 2015-11-12 | Evonik Degussa Gmbh | Herstellung eines auf Stahl und Polyurethan basierenden Faserverbundbauteils |
| DE102014209183A1 (de) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Reaktive Zusammensetzung aus einer Uretdiongruppen haltigen Dispersion und Polyaminen |
| EP2947106A1 (fr) | 2014-05-15 | 2015-11-25 | Evonik Industries AG | Composition réactive d'une dispersion contenant des groupes uretdiones et polyamines |
| EP2977395A1 (fr) | 2014-07-21 | 2016-01-27 | Evonik Degussa GmbH | Compositions de polyurethane hautement reactives a base de groupes uretdione contenant des sels carbonate |
| DE102014214130A1 (de) | 2014-07-21 | 2016-01-21 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten |
| WO2016016069A1 (fr) | 2014-07-28 | 2016-02-04 | Evonik Degussa Gmbh | Production efficace de semi-produits et de composants composites dans le procédé d'application de pression par voie humide en utilisant des (méth)acrylates fonctionnalisés par un hydroxy, qui sont réticulés de manière thermodurcissable au moyen d'isocyanates ou d'uretdiones |
| EP2979851A1 (fr) | 2014-07-28 | 2016-02-03 | Evonik Degussa GmbH | Fabrication efficace de demi-produits et composants composites dans le cadre du procédé de pressage à froid utilisant des (méth)acrylates hydroxyfonctionnalisés réticulés par duroplastie à l'aide d'isocyanates ou d'uretdions |
| EP2993202A1 (fr) | 2014-09-08 | 2016-03-09 | Evonik Degussa GmbH | Demi-produits composites et pièces moulées en étant constituées ainsi que pièces moulées directement fabriquées à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdions réticulés par duroplastie |
| EP3124515A1 (fr) | 2015-07-28 | 2017-02-01 | Evonik Degussa GmbH | Dispersions reactives non aqueuses pour peintures, materiaux d'etancheite et adhesifs |
| EP3138685A1 (fr) | 2015-09-03 | 2017-03-08 | Evonik Degussa GmbH | Composant hybride dote d'un renfort local constitue d'un materiau en fibres composites a base de polyurethane, reticule en deux etapes |
| US10245789B2 (en) | 2015-09-03 | 2019-04-02 | Evonik Degussa Gmbh | Hybrid component part comprising a local stiffening composed of a two-stage-crosslinked polyurethane-based fibre composite material |
| EP3330311A1 (fr) | 2016-12-02 | 2018-06-06 | Evonik Degussa GmbH | Préimprégné de monocomposant polyuréthane stable au stockage et corps moulés ainsi fabriqués à partir de ladite composition de polyuréthane |
| US10626236B2 (en) | 2016-12-02 | 2020-04-21 | Evonik Operations Gmbh | Storage-stable one-component polyurethane prepregs and shaped bodies composed of polyurethane composition that have been produced therefrom |
| WO2019175714A1 (fr) | 2018-03-16 | 2019-09-19 | 3M Innovative Properties Company | Compositions, procédé de collage et assemblage |
| WO2019175709A1 (fr) | 2018-03-16 | 2019-09-19 | 3M Innovative Properties Company | Compositions, procédé de liaison et ensemble lié |
| EP3560971A1 (fr) | 2018-04-27 | 2019-10-30 | Evonik Degussa GmbH | Système à matrice hybride à deux composants de polyuréthanes et de polyméthacrylates destiné à la fabrication de demi-produits renforcés par des fibres courtes |
| EP3572446A1 (fr) | 2018-05-24 | 2019-11-27 | Evonik Degussa GmbH | Mélange réactif d'uretdiones et de catalyseurs |
| WO2020065456A1 (fr) | 2018-09-25 | 2020-04-02 | 3M Innovative Properties Company | Composition thermodurcissable en une partie |
| CN109574934A (zh) * | 2018-12-21 | 2019-04-05 | 六安科瑞达新型材料有限公司 | 一种脂肪族脲二酮的制备方法 |
| EP3929233A1 (fr) | 2020-06-25 | 2021-12-29 | Evonik Operations GmbH | Compositions de polyuréthane réactives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3739549A1 (de) | 1989-06-01 |
| JPH01160960A (ja) | 1989-06-23 |
| ATE97659T1 (de) | 1993-12-15 |
| EP0317744A3 (en) | 1990-10-10 |
| DE3739549C2 (de) | 1994-10-27 |
| DE3885859D1 (de) | 1994-01-05 |
| JP2601530B2 (ja) | 1997-04-16 |
| EP0317744A2 (fr) | 1989-05-31 |
| CA1274835A (fr) | 1990-10-02 |
| EP0317744B1 (fr) | 1993-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4912210A (en) | Process for the preparation of (cyclo)aliphatic uretediones | |
| US4929724A (en) | Process for the production of uretdione group-containing compounds, the compounds obtained according to this process and the use thereof in the production of polyurethane plastics material | |
| US4476054A (en) | Uretidione dimer of isophorone diisocyanate and method of preparation | |
| JP2849932B2 (ja) | ウレツトジオン基及びイソシアヌレート基を含有する変性ポリイソシアネート並びに二成分系ポリウレタン被覆用組成物 | |
| JP4490813B2 (ja) | ウレトジオン基を含むイソシアネート | |
| JP3103630B2 (ja) | ウレットジオン基及び／又はイソシアヌレート基を含有するポリイソシアネート並びにそれらの製造方法 | |
| EP0671426A1 (fr) | Mélanges de polyisocyanate (cyclo)aliphatique modifiés, procédé pour leur préparation et leur utilisation | |
| US4613686A (en) | Process for the preparation of polyisocyanates with biuret structure | |
| US6452003B1 (en) | Process for preparing low-odor and storage-stable monomer-containing polyisocyanurates from isophorone diisocyanate | |
| JPH0315634B2 (fr) | ||
| US6093817A (en) | Process for preparing a reduced-color isocyanurate-functional polyisocyanate prepared from 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI) | |
| JPH09208563A (ja) | ウレトジオンジイソシアネート及びその製造方法 | |
| US5149766A (en) | Process for the preparation of uretdione group containing polyisocyanates | |
| KR100566025B1 (ko) | 담색우레트디온폴리이소시아네이트의제조방법 | |
| JP2009137961A (ja) | ウレトジオンポリイソシアネートの製造 | |
| US20030135007A1 (en) | Catalysts for preparing polyisocyanates containing isocyanurate groups, and their use | |
| JPH11140157A5 (fr) | ||
| EP4570843A1 (fr) | Composition de diisocyanate d'isophorone et produit bloqué de celle-ci | |
| US20210206730A1 (en) | Process for preparing isocyanurate | |
| US4263221A (en) | Process for the preparation of aromatic carbodiimides | |
| JPH09188742A (ja) | 無色ウレトジオン及びその製法 | |
| US5929241A (en) | Process for the preparation of an isocyanate-free uretdione of isophorone diisocyanate | |
| US5258508A (en) | Process for the preparation of oligomeric polyisocyanates and their use | |
| CA2413642A1 (fr) | Catalyseurs pour la preparation de polyisocyanates contenant des groupes isocyanurates et leur utilisation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: HUELS AKTIENGESELLSCHAFT, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:DISTELDORF, JOSEF;HUEBEL, WERNER;SCHMITZ, KARL;REEL/FRAME:005237/0604;SIGNING DATES FROM 19891117 TO 19891125 |
|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| FPAY | Fee payment |
Year of fee payment: 8 |
|
| FEPP | Fee payment procedure |
Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| AS | Assignment |
Owner name: DEGUSSA-HUELS AKTIENGESELLSCHAFT, GERMANY Free format text: MERGER;ASSIGNOR:HUELS AKTIENGESELLSCHAFT;REEL/FRAME:011837/0001 Effective date: 19990201 |
|
| FPAY | Fee payment |
Year of fee payment: 12 |
|
| AS | Assignment |
Owner name: DEGUSSA AG, GERMANY Free format text: CHANGE OF NAME;ASSIGNOR:DEGUSSA-HUELS AKTIENGESELLSCHAFT;REEL/FRAME:012463/0601 Effective date: 20010209 |